Sandmeyer Reaction

The Substitution Of An Aromatic Amino Group Is Possible Via Preparation Of Its Diazonium Salt And Subsequent Displacement With A Nucleophile (Cl-, I-, CN-, RS-, HO-). Many Sandmeyer Reactions Proceed Under Copper(I) Catalysis, While The Sandmeyer-type Reactions With Thiols, Water And Potassium Iodide Don't Require Catalysis.

The Sandmeyer Reaction Is A Very Important Transformation In Aromatic Chemistry, Because It Can Result In Some Substitution Patterns That Are Not Achievable By Direct Substitution.

Fluorination Is Possible By Using The Related  Schiemann Reaction.

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Mechanism Of The Sandmeyer Reaction

Recent Literature

Catalytic Sandmeyer Bromination
I. P. Beletskaya, A. S. Sigeev, A. S. Peregudov, P. V. Petrovskii, Synthesis, 2007, 2534-2538.

Halo- And Azidodediazoniation Of Arenediazonium Tetrafluoroborates With Trimethylsilyl Halides And Trimethylsilyl Azide And Sandmeyer-Type Bromodediazoniation With Cu(I)Br In [BMIM][PF₆] Ionic Liquid
A. Hubbard, T. Okazaki, K. K. Laali, J. Org. Chem., 2008, 73, 316-319.

Unusually Stable, Versatile, And Pure Arenediazonium Tosylates: Their Preparation, Structures, And Synthetic Applicability
V. D. Filimonov, M. Trusova, P. Postnikov, E. A. Krasnokutskaya, Y. M. Lee, H. Y. Hwang, H. Kim, K.-W. Chi, Org. Lett., 2008, 10, 3961-3964.

One-Pot, Metal-Free Conversion Of Anilines To Aryl Bromides And Iodides
D. A. Leas, Y. Dong, J. L. Vennerstrom, D. E. Stack, Org. Lett., 2017, 19, 2518-2521.

Sulfonic Acid Based Cation-Exchange Resin: A Novel Proton Source For One-Pot Diazotization-Iodination Of Aromatic Amines In Water
V. D. Filimonov, N. I. Semenischeva, E. A. Krasnokutskaya, A. N. Tretyakov, H. Y. Hwang, K.-W. Chi, Synthesis, 2008, 185-187.

A New, One-Step, Effective Protocol For The Iodination Of Aromatic And Heterocyclic Compounds Via Aprotic Diazotization Of Amines
E. A. Krasnokutskaya, N. I. Semenischeva, V. D. Filimonov, P. Knochel, Synthesis, 2007, 81-84.

A Highly Efficient Cu-Catalyzed S-Transfer Reaction: From Amine To Sulfide
Y. Li, J. Pu, X. Jiang, Org. Lett., 2014, 16, 2692-2695.

In A Copper-free Sandmeyer-type Fluorosulfonylation Reaction With Na₂S₂O₅ as The Sulfur Dioxide Source And Selectfluor As Fluorine Source, Aryldiazonium Salts Are Transformed Into Sulfonyl Fluorides. In Situ Diazotization Enables The Use Of Aromatic Amines As Substrates. The Method Offers Broad Functional Group Tolerance, Gram-scale Synthesis And Late-stage Fluorosulfonylation.
T. Zhong, M.-K. Pang, Z.-D. Chen, B. Zhang, J. Weng, G. Lu, Org. Lett., 2020, 22, 2941-2945.

Methanol-Promoted Borylation Of Arylamines: A Simple And Green Synthetic Method To Arylboronic Acids And Arylboronates
C.-J. Zhao, D. Xue, Z.-H. Jia, C. Wang, J. Xiao, Synlett, 2014, 25, 1577-1584.

Sandmeyer Trifluoromethylation
G. Danoun, B. Bayermagnai, M. F. Grünberg, C. Matheis, E. Risto, L. J. Gooßen, Synthesis, 2014, 46, 2283-2286.

Copper-Promoted Sandmeyer Trifluoromethylation Reaction
J.-J. Dai, C. Fang, B. Xiao, J. Yi, J. Xu, Z.-J. Liu, X. Lu, L. Liu, Y. Fu, J. Am. Chem. Soc., 2013, 135, 8436-8439.

Metal-Free Aromatic Carbon-Phosphorus Bond Formation Via A Sandmeyer-Type Reaction
S. Wang, D. Qiu, F. Mo, Y. Zhang, J. Wang, J. Org. Chem., 2016, 81, 11603-11611.